The major themes of Winesburg, Ohio largely concern the interaction between the individual citizens of Winesburg and the world around them. As each of the book's stories focuses primarily (though not exclusively) on one character, the narrator develops these themes continuously, sometimes adding new insights about previously introduced characters (Elizabeth Willard's relationship with Dr. Reefy in "Death", for example, was never alluded to when she was first introduced in "Mother".). Because George Willard is a fixture in much of the book, his character arc becomes just as important a theme of Winesburg, Ohio as that of the rest of town's inhabitants.
Inability to communicate, loneliness, and isolation
The most prevalent theme in Winesburg, Ohio is the interplay between how the Winesburg citizens' "...inability to translate inner feelings into outward form" expresses itself in the loneliness and isolation that makes their various adventures noteworthy. This dynamic is present, in some form, in practically all of the stories, two fairly representative examples being the merchant's son, Elmer Cowley, in the story "Queer", George's mother, Elizabeth Willard, in the stories, "Mother" and "Death," and Jessie Bentley in "Godliness."
In the former, the young man, Elmer Cowley, incited by an imagined slight ("He thought that the boy who passed and repassed Cowley & Son's store ...must be thinking of him and perhaps laughing at him" when in reality, "[George] had long been wanting to make friends with the young merchant...") tries twice to tell George off but is unable to communicate his feelings either time, finally physically assaulting the young reporter. The story ends with Cowley telling himself, " 'I showed him...I guess I showed him. I guess I showed him I ain't so queer", a proclamation obviously laced with dramatic irony.
In the latter two stories, Elizabeth Willard was the "tall and gaunt...ghostly figure [moving] slowly through the halls..." of the New Willard House who eventually, in "Death", succumbs to illness. In her youth, Elizabeth "...had been 'stage-struck' and, wearing loud clothes, paraded the streets with traveling men from her father's hotel". She was a character who, "perhaps more than any of the other characters, seeks some kind of release from her perpetual loneliness". And yet, aside from her very brief love affair with Dr. Reefy, Elizabeth Willard finds no solace. Instead, both of her stories conclude with Elizabeth Willard attempting to communicate with her son but, like the dumbfounded Elmer Cowley, winding up unsuccessful.
In contrast with the stark view of Winesburg, Ohio above, a number of scholars have taken the perspective that the cycle is, in fact, about escape from isolation instead of the condition itself. Barry D. Bort writes, "Criticism of Winesburg, Ohio has recognized this desperate need to communicate, but what has not been understood about Anderson's work is that this continual frustration serves as the context out of which arise a few luminous moments of understanding...Such moments are at the heart of Winesburg, Ohio, although they are few and evanescent". Though rarely does escape come in the narrative present, many of the stories prominently feature anecdotes of past adventures where lonely and reserved characters run naked through the town on a rainy night (Alice Hindman in "Adventure"), drive their wagon headlong into a speeding locomotive (Windpeter Winters in "The Untold Lie"), and have window-shattering religious epiphanies (Reverend Curtis Hartman in "The Strength of God"). While not all of the adventures are so dramatic, each has its place in the annals of the town, sometimes as told to George Willard, other times in the memories of participants.
George Willard's coming-of-age
George Willard, a young reporter for the Winesburg Eagle, figures prominently in much of Winesburg, Ohio.[note 2] Throughout the book, he plays the dual role of listener and recorder of other people's stories and advice, and the young representative of the town's hopes whose coming-of-age reaches its dénouement in the final tale, "Departure", when George leaves Winesburg for the city. Much of George's story is centered around two interconnected threads: those of his sexual and artistic maturation. Most of the time, these two formative elements proceed together; it is solely when George loses his virginity to Louise Trunnion in "Nobody Knows" that the adventure is exclusively sexual. Afterwards, starting with his desire to fall in love with Helen White in order to have material for a love story in "The Thinker", the desire for sexual fulfillment becomes linked to his literary/emotional sensibility.
In "The Teacher", a central point in George's development, "Kate Swift, George's school teacher, realizes his literary potential..." and tries to communicate her thoughts to George but, "...his sexual desire kindles her own, and she loses touch with the intellectual, spiritual, and creative potentials of her emotion. At last, however, George begins to perceive that there is something more to be communicated between men and women than physical encounter..." Yet this lesson is not solidified for the young reporter when, after boasting in a bar in the story "An Awakening", he has a surge of "masculine power" and tries to seduce Belle Carpenter, only to be repelled and humiliated by her beau, the large-fisted bartender, Ed Handby.
The climax of George's sexual and artistic coming-of-age comes in the second-to-last story of the collection, "Sophistication". Early in the story, while walking amongst the crowds of the Winesburg County Fair, George felt "...a thing known to men and unknown to boys. He felt old and little tired...[and]...he wanted someone to understand the feeling that had taken possession of him after his mother's death [an event that took place in, "Death", the previous story]". That someone turned out to be Helen White, who herself had "...come to a period of change". It is in the time they spend together that readers see "his acceptance of Helen as a spiritual mediator..." which signifies that "...George's masculinity is balanced by the feminine qualities of tenderness and gentleness, an integration that Anderson suggests is necessary for the artist."